Cas no 5453-86-1 (Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate)

Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate is a nitro-substituted benzisoxazole derivative with significant utility in organic synthesis and pharmaceutical research. Its key advantages include its role as a versatile intermediate in the preparation of heterocyclic compounds, owing to the reactivity of both the nitro and ester functional groups. The benzisoxazole core provides a stable scaffold for further chemical modifications, while the electron-withdrawing nitro group enhances electrophilic substitution reactions. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules, including potential therapeutic agents. Its well-defined structure and synthetic accessibility make it a reliable building block for advanced chemical applications.
Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate structure
5453-86-1 structure
Product Name:Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate
CAS No:5453-86-1
MF:C9H6N2O5
MW:222.15434217453
CID:379457
PubChem ID:227352
Update Time:2025-10-29

Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1,2-Benzisoxazole-3-carboxylicacid, 6-nitro-, methyl ester
    • METHYL 6-NITRO-1,2-BENZISOXAZOLE-3-CARBOXYLATE
    • methyl 6-nitro-1,2-benzoxazole-3-carboxylate
    • BEN175
    • Methyl 6-nitrobenzo[d]isoxazole-3-carboxylate
    • methyl 6-nitrobenzisoxazole-3-carboxylate
    • FT-0735680
    • 5453-86-1
    • DTXSID60280841
    • NSC18904
    • METHYL6-NITRO-1,2-BENZISOXAZOLE-3-CARBOXYLATE
    • D76376
    • A913740
    • SCHEMBL17437900
    • RDAMDINPNCIMJD-UHFFFAOYSA-N
    • AKOS005082253
    • MFCD00083016
    • 1G-437S
    • METHYL-5-NITRO BENZ ISOXAZOLE-2-CARBOXYLATE
    • NSC 18904
    • CS-0103847
    • NSC-18904
    • Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate
    • Inchi: 1S/C9H6N2O5/c1-15-9(12)8-6-3-2-5(11(13)14)4-7(6)16-10-8/h2-4H,1H3
    • InChI Key: RDAMDINPNCIMJD-UHFFFAOYSA-N
    • SMILES: O1C2C=C(C=CC=2C(C(=O)OC)=N1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 222.02800
  • Monoisotopic Mass: 222.028
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 303
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.7
  • Topological Polar Surface Area: 98.2?2

Experimental Properties

  • Density: 1.487
  • Boiling Point: 389 °C at 760 mmHg
  • Flash Point: 189 °C
  • Refractive Index: 1.625
  • PSA: 98.15000
  • LogP: 2.04580

Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate Pricemore >>

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Additional information on Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate

Recent Advances in the Study of Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate (CAS: 5453-86-1)

Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate (CAS: 5453-86-1) is a chemical compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its nitro-substituted benzisoxazole core, has been explored for its potential applications in drug discovery and development. Recent studies have focused on its synthesis, biological activity, and potential therapeutic uses, making it a subject of interest for researchers aiming to develop novel pharmacological agents.

The synthesis of Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate has been optimized in recent years to improve yield and purity. Researchers have employed various catalytic and non-catalytic methods, including microwave-assisted synthesis, to achieve efficient production. These advancements have facilitated the compound's availability for further biological evaluation. The compound's structural features, particularly the nitro group and the benzisoxazole moiety, are believed to contribute to its reactivity and potential interactions with biological targets.

In terms of biological activity, Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate has shown promise in preliminary studies as an inhibitor of specific enzymes involved in inflammatory and oncogenic pathways. For instance, recent in vitro assays have demonstrated its ability to modulate the activity of cyclooxygenase-2 (COX-2) and certain kinases, suggesting potential applications in anti-inflammatory and anticancer therapies. However, further in vivo studies are required to validate these findings and assess the compound's pharmacokinetic and toxicological profiles.

Another area of interest is the compound's potential role in the development of prodrugs. The ester functional group in Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate can be hydrolyzed under physiological conditions, releasing active metabolites. This property has been exploited in the design of prodrugs aimed at improving drug delivery and bioavailability. Recent research has explored the coupling of this compound with various therapeutic agents to enhance their efficacy and reduce side effects.

Despite these promising developments, challenges remain in the clinical translation of Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate. Issues such as solubility, stability, and potential toxicity need to be addressed through systematic preclinical studies. Additionally, the compound's mechanism of action at the molecular level requires further elucidation to optimize its therapeutic potential. Collaborative efforts between chemists, biologists, and pharmacologists will be essential to overcome these hurdles.

In conclusion, Methyl 6-nitro-1,2-benzisoxazole-3-carboxylate (CAS: 5453-86-1) represents a versatile scaffold with significant potential in drug discovery. Recent advancements in its synthesis and biological evaluation have laid the groundwork for future research. As the understanding of its pharmacological properties deepens, this compound may pave the way for the development of novel therapeutic agents targeting a range of diseases. Continued investment in research and development will be crucial to unlocking its full potential.

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